0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content. Method 7: Cycloaddition Reactions Involving Carbon Diselenide

DOI: 10.1055/sos-SD-018-00070

Braverman, S.; Cherkinsky, M.; Birsa, M. L.Science of Synthesis, (200518246.

While 1,3-heterocumulenes do not comply with the definition of 1,3-dipolar compounds, they can undergo [3+2]-cycloaddition reactions with alkynes. In contrast to 1,3-dipolar compounds, which lead to saturated or unsaturated five-membered heterocycles, reactions of carbon diselenide with alkynes having electron-withdrawing substituents provide nucleophilic carbenes. These are unstable and dimerize to the corresponding tetraselenafulvalenes 540, usually as a mixture of cis- and trans-isomers (Scheme 270).[‌1114‌,‌1115‌] Carbon diselenide has been found to be more reactive toward alkynyl compounds than carbon disulfide.[‌1116‌]

Meeeee 888 [8+8]-Meeeeeeeeeeee Meeeeeeee ee Meeeee Meeeeeeeee[‌8888‌‌8888‌]

Meeeee eeeeeeeeee eee eeee eeeeeeeee ee e eeeeee ee eeeeee eeeeeeee eeeeeeeeeeee eeeeee eee eeeeeeee eeee ee-eeee-eeeeeeeeeeeeeeeee.[‌8888‌] Meeeee eeeeeeeeee ee eeee eeeeeee ee [8+8]-eeeeeeeeeeeee eeeeeeeee. Meeeeeee eeee (eeee-eeeeeeeeee)(8,8,8,8-eeeeeeeeeeeeeeeeeeeee)eeeeee eeeee ee eee eeeeeeeeeeeee eeeeeeeeeee 8,8,8-eeeeeeeeeeeeeeeeeee.[‌8888‌]